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Synthesis and Self-Assembly of Dihydroxyperylene Bisimides for the Tuning of Photophysical Properties

Authors

  • Dr. Yongjun Li,

    Corresponding author
    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China), Fax: (+86) 10-82616576
    • Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China), Fax: (+86) 10-82616576

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  • Zhihong Qing,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China), Fax: (+86) 10-82616576
    2. Graduate University of Chinese Academy of Sciences, Beijing 100190 (P.R. China)
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  • Yanwen Yu,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China), Fax: (+86) 10-82616576
    2. Graduate University of Chinese Academy of Sciences, Beijing 100190 (P.R. China)
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  • Taifeng Liu,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China), Fax: (+86) 10-82616576
    2. Graduate University of Chinese Academy of Sciences, Beijing 100190 (P.R. China)
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  • Runsheng Jiang,

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China), Fax: (+86) 10-82616576
    2. Graduate University of Chinese Academy of Sciences, Beijing 100190 (P.R. China)
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  • Prof. Yuliang Li

    1. Beijing National Laboratory for Molecular Sciences (BNLMS), CAS Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (P.R. China), Fax: (+86) 10-82616576
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Abstract

The synthesis of 1,10-dihydroxyperylene bisimides by nucleophilic substitution of brominated perylene bisimide is described. 1,10-Dihydroxyperylene bisimides formed J aggregates in nonpolar solvents and showed a clearly redshifted absorption band. The solvent polarity also influenced the hydrogen bond with the hydroxyl group, and thus, the photophysical properties of perylene bisimide. The photophysical properties of these dihydroxyperylene perylene bisimides can also be tuned by changing charge transfer from the hydroxyl groups to the perylene core through the introduction of metal ions.

Abstract

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